


you can be my wingman anytime

by StarAmongStones



Category: Teen Wolf (TV)
Genre: Fluff, Friends to Lovers, Future Fic, M/M, background scisaac if you squint, derek just kind of fails at life
Language: English
Status: Completed
Published: 2013-09-15
Updated: 2013-09-15
Packaged: 2017-12-26 14:49:51
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,656
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/967225
Author URL: https://archiveofourown.org/users/StarAmongStones/pseuds/StarAmongStones
Summary: <blockquote class="userstuff">
              <p>
  <i>“I need a wingman, and you owe me for that one time I set you up with my R.A.”</i>
</p><p> </p><p>  <i>Blinking, Derek replies slowly, “She told me she was in love with me on our second date. And asked if it would be okay for her to move in with me on our third.”</i></p><p> </p><p>  <i>“Okay, that is just your own fault for even going on a third date."</i></p>
            </blockquote>





	you can be my wingman anytime

“Alright, here’s the deal,” Stiles says, barging into the loft one evening without even knocking. It says something about Derek’s life that this doesn’t even register as weird anymore.

“The deal,” Derek prompts from the kitchen doorway when Stiles abruptly stops in the middle of the room.

“Literally what is happening.”

Derek is confused for a moment, until he follows Stiles’ gaze to the bright pink apron he’s currently wearing. He shrugs, feels the tips of his ears burn traitorously, and mumbles, “Cora made it for me.”

Stiles’ expression shifts into something soft for a moment before he huffs out a laugh. “WORLD – S – BEST BETA?”

“She ran out of room,” Derek explains why the “S” – in purple puff paint, no less – is below the word “WORLD” and not on the end of it.

“Fucking Cora,” Stiles laughs fondly. “How was move-in?”

 “She didn’t tell you?”

“No, she told me. I just want to know how you think it went,” Stiles steps closer, face carefully neutral.

Derek lifts his left shoulder in a slight shrug, feeling a sudden wave of loneliness. He helped her move into her new apartment two days ago, but he still hasn’t gotten used to her being gone again. The stupid thing is that this is her third year in college, and he should be over the empty nest syndrome by now.

“Thought so,” Stiles replies gently. He moves past Derek to take a seat at the kitchen table, and continues, “This is good, actually. I need you to do me a favor, which is really a favor to you because it’ll get your mind off everything for a while. Here’s the deal: you’re going to be my wingman tonight.”

Derek raises his eyebrows, and folds his arms over his chest.                       

Stiles rolls his eyes, and says, “You know I’m literally never going to take you seriously again, right?” as he gestures towards Derek’s apron.

Derek refuses to take it off because it was a gift, and Stiles must never win.

They stare at each other until the younger man caves. He has never been able to wait Derek out, and they both know it.

“Dude, you owe me for that one time I set you up with my R.A.”

Blinking, Derek replies slowly, “She told me she was in love with me on our second date. And asked if it would be okay for her to move in with me on our third.”

“Okay, that is just your own fault for even going on a third date,” Stiles shrugs, enjoying the shit out of the situation as always.

“You’ve been single for twenty years,” Derek attempts to steer the conversation away from his horrific dating life, “what difference does one more make?”

“Actually,” Stiles starts a bit testily, “I was single for seventeen, and then again for three more years. And it’s just different, okay? Have a heart, man. Weren’t you young and horny once?”

He visibly winces at the implication, but Derek shrugs it off as best he can.

“Why the sudden rush?” Derek eventually asks, alleviating Stiles of his embarrassment.

Stiles groans quietly, “I don’t know. I’ve just been feeling weird about it recently. Does there really have to be a reason?”

Derek shrugs. He supposes not.

When Stiles flicks his gaze back to him, the boy’s face is so fucking hopeful that Derek just can’t say no. When Stiles realizes this, his eyes widen in excitement.

“Pick you up at ten!” Stiles calls over his shoulder as he bounds out the door like he’s afraid Derek will change his mind and say no. To be fair, Derek thinks he probably had a fifty-fifty chance of doing just that.

* * *

“So, here we are. Doing this. Yep,” Stiles taps his fingers against his thigh, scanning the dimly-lit, slightly smoky room in front of them. They compromised and went to a jazz club downtown, so it was a little sparsely populated, but not too bad.

“Pick,” Derek prompts, when Stiles doesn’t move fast enough for his taste. It’s possible he’s a little grumpy, but he had originally planned to watch _People Like Us_ for the seventh time that week and wallow in self-pity, so he can hardly be blamed.

Stiles glances over at him, and physically shakes his head. He quietly mutters to himself, “Alright, you can do this. Come on,” and starts scanning the room in earnest.

Finally, after another couple of minutes – in which Derek passive-aggressively checks his watch half a dozen times – he points to the cute blonde who had walked in just behind them, shrugging, “Her, I guess.”

“You have such a discerning palate,” Derek drawls, and Stiles snorts.

“Yeah, yeah. Just go talk me up, get me a number, and you can get back to crying in your Chunky Monkey.”

“I would never,” Derek protests, even though he knows Stiles knows about his secret stash behind the frozen vegetables.

Stiles pushes him lightly, and Derek allows himself to be corralled towards the bar while Stiles hangs back to wait for his cue.

He stops right next to the girl, and she flashes him a brief smile after very obviously running her eyes down his body. Good, he’s got an in. He opens his mouth and – nothing. Literally nothing comes out. What the fuck.

The girl’s smile turns smug, and she says, “Maybe when you’re older, hon,” which is actually just really confusing because he is pretty sure he’s older than her.

He turns towards Stiles, baffled. Stiles grins, and pushes his way through the masses.

“Dude, what the hell was that? You just kind of,” Stiles searches for a word, “gaped.”

“I-“

“I’ve seen you flirt before. I know you’re capable,” Stiles cuts him off, unable to contain his laughter anymore.

“I don’t –“

“You know what? That was so entertaining I can’t even be mad about this whole thing being a waste of time,” he claps Derek’s shoulder, steering him back out into the night.

“But we just got here,” Derek says once they’re back at the jeep, deeply confused about the point of all this if they were just going to throw in the towel after one try.

Stiles freezes. Dawning comprehension plays across his features, which Derek isn’t even going to try to touch because something is clearly wrong with the world tonight and he’s stopped pretending he’ll ever catch up to what’s going on.

Stiles whispers, “Oh,” and his heartbeat picks up slightly.

Derek pulls on the still-locked door handles, looking pointedly at Stiles.

“Right!” Stiles startles. He steals glances at Derek the whole way home, while Derek stares straight ahead and makes a mental note to never address anything ever again.

* * *

“Come on,” Derek growls, tugging at Stiles’ wrist a few nights later before he can even open his door all the way, “we’re going out.”

“Woah, what?” Stiles slams his door with a quick, “Don’t wait up!” to Scott, tripping down the hall after Derek.

Clearly the question doesn’t mean that much to him because he doesn’t ask again. Once seated in the car, though, Stiles muses, “You know, this is basically exactly how I thought it would go. Right down to the anger and forcefulness, even. You, sir, are pretty predictable.”

Derek grunts in response, too focused on his game plan – a.k.a. the plan to get Stiles laid. And yes, Derek likes calling it his _game_ plan in his head because he can appreciate a good pun and he had never realized until that very moment that Stiles has probably rubbed off on him way more than he realized. Awesome.

“I have game,” Derek mutters to himself with faked conviction. Visualize positive outcomes and all that.

Stiles’ heartbeat kicks up a notch as he laughs, and says, “Uh, you really don’t.”

At Derek’s glare, Stiles throws up his hands in a placating gesture immediately.

“No, it’s cute. Really. I mean, obviously I like it,” Stiles smiles gently. It’s weird.

“Your heartbeat is faster than normal. It’s distracting,” Derek says instead of going anywhere near whatever the hell is going on with Stiles today.

“Sorry,” Stiles snorts. “I’ll keep an eye on it.”

His heartbeat picks up even more. Derek suspects he’s just doing it on purpose now.

When they pull up outside a sketchy dive bar in the next town over, Stiles lights up. Recognizing the place as one the deputies never go to, he asks, “Does this mean I can drink?” as he clambers out of the car.

“Don’t tell your dad. I’d rather not get fired,” he answers. He’s also deathly afraid of the sheriff’s Disappointed Father look, but no one has to know that.

“Best date ever,” Stiles punches his arm lightly, whipping out his fake I.D. It makes Derek feel a little better when it turns out to be unnecessary because no one ever checks that they’re over 21. And then he feels guilty that he, as a fairly new officer of the law, feels good about that.

“It’s not a date yet,” Derek says distractedly. He makes his way to two empty bar stools before asking, “Okay, who looks interesting?”

“What?”

Derek gestures determinedly towards the rest of the room in a sweeping motion, “I am going to get you a date if it kills me. Pick. I can do it for you, but there’s a chance you won’t like him or her. But pick a him. I think I might have tripped up because the last person was a woman.” God knows he has a weakness for pretty ladies.

“You lost me. Is this some sort of fucked-up test? Because dude-”

“Fine, that guy it is,” Derek cuts him off, pointing down to the other end of the bar. The guy is cute enough: dark-haired, wiry, well-dressed. He remembers Stiles saying something about suspenders being an interesting sartorial choice a while ago, but he couldn’t recall if that was a good or bad thing. He supposes he’ll know soon enough.

Derek saunters towards the guy, leaving a sputtering Stiles behind. When he gets there, he leans casually against the bar, an appropriate distance between them, and says, “My friend likes your suspenders,” taking a shot.

“Uh,” the guy startles, confused, “thanks?”

“He’s,” Derek begins, but blanks. Again. How is he supposed to finish that sentence? Stiles is so many things – loyal, annoying, the person Derek has been closest to for a while now, kind of a dick – that there’s almost too much Derek could say about him.

His brain kind of short-circuits for a moment. Finally, he says, “He’s in college,” gesturing to where Stiles is hopping down from his seat. Derek winces slightly at just how incredibly stupid he sounds. How is it so easy to flirt for his own purposes, but when he tries to do it for someone else he turns into a train wreck who has never talked to another human being before?

“That’s nice,” the guy says slowly, edging his back towards Derek and taking a pointed sip of his martini. Who even drinks martinis anyway?

“Sorry about him,” Stiles tells the man. Derek bristles slightly because he’s trying his best, okay? But he lets himself be dragged out of the bar by the hand.

Instead of dropping Stiles’, Derek curls his fingers a little tighter and pulls back gently, making Stiles stop and turn.

“Why do we keep leaving after one try? I can do this, I swear. I’m just – I’m a little rusty,” he rolls his shoulders, preparing to head back in.

Stiles smiles fondly, and replies, “You don’t have to do this, you know. I get it, and I’m actually good with it. Very pro this.”

“This what?” Derek shakes his head in confusion. It’s like they’ve been having two conversations lately. Derek honestly expects he will punch a wall by the end of the week out of sheer frustration.

“Okay, have it your way,” Stiles sighs, dropping Derek’s hand. It’s only then that he realizes they had been essentially holding hands the entire conversation. “We do have to talk about this sometime, though. I get that you’re categorically allergic to feelings or whatever, but I don’t care. Also, you do realize this would have been so much easier if you had just told me with your words instead of doing some bass ackwards demonstration.”

Derek makes a non-committal sound. He doesn’t really understand what’s going on here, but a lot of the time it’s just easier to let Stiles talk himself out.

“Hey, can we actually go to your place?” Stiles breaks the silence when they’re about half-way back to his apartment. “Scott texted me about some alone time with Isaac when you were, you know, doing your thing back there. Sorry, I almost forgot to ask.” 

Derek easily u-turns back towards the loft without a word. He and Stiles developed a system a while back where the couch was all his when one of his roommates wanted to have a date over. It had started back at the dorms when Stiles’ pot-luck roommate, who was so unremarkable that none of them even remembers his name, had some sort of orgy in their room at two in the afternoon. The details are a little fuzzy. Stiles doesn’t like to talk about it.

“Hey!” Stiles yells delightedly from the bathroom once they’re back at the loft. Poking his head back through the doorway, he finishes, “You kept my toothbrush.”

Shrugging because it’s not that big a deal, Derek hands Stiles his own pair of sweats and a t-shirt. Stiles has commandeered the bottom drawer of Derek’s dresser for exactly situations like this.

“Oh,” Stiles stares down at the pile, “right. Yeah, good idea. I was up until three finishing my anthropology paper anyway.”

Derek stares at the newly closed door. Okay. Shaking his head, he turns away throw his shirt and jeans into the hamper, and slide under the sheets in his boxers. Normally he sleeps naked, but never when Stiles is over because for some reason he just feels really weird about it.

Stiles emerges a few minutes later, and smiles softly down at Derek. Instead of turning right towards the couch, he slides in next to the Derek, snuggling closer until his head is resting on the older man’s left shoulder, right arm slung low across Derek’s waist.

Well, that was unexpected.

“Relax,” Stiles orders against his collarbone. Then, stiffening in turn, he asks, “Unless this is too much?”

That’s what makes Derek finally ease into the touch. Derek is out of practice with being so close to someone else, but he used to be a really tactile person when he was younger. Sometimes he misses it, and this is kind of nice. Weird and new, but nice.

“It’s fine,” Derek assures him at last. He rests his cheek on top of Stiles’ hair, and lets his arms come up to more comfortably rest around Stiles’ ribcage as they both drift off.

* * *

“Whatcha got for me, Waffles?” Stiles mutters sleepily from the entrance into the kitchen the next morning. He leans against the doorframe, lightly scratching at his sleep-tousled hair, smiling warmly.

“No waffles, just French toast,” Derek grins at Stiles’ groan.

“That joke wasn’t funny the first time, and it’s still not,” Stiles pretends to scold, but he’s smiling too hard for any real heat to be behind it.

“Your nickname wasn’t funny the first time either, but do you see me complaining?”

“You complain all the time. And that nickname is genius because really, who hates waffles? It’s just weird.”

“Food shouldn’t have pockets.”

Derek privately enjoys the bright laughter behind him. They’ve had this conversation almost every time they eat breakfast together, and yet Stiles always laughs like it’s the first time. He starts to wonder what else Stiles does every time like it’s the first time, and nope. It’s way too early to go places that Derek steadfastly refuses to ever go ever.

He divvies up the eggs as Stiles pours himself a cup of coffee, and Derek some orange juice.

After the first bite, Stiles moans around his fork and his eyes slide closed.

“Good?” Derek raises an amused eyebrow.

“I think I just saw the face of God,” Stiles answers around a mouthful of food.

Derek snorts, and they fall into companionable silence. They don’t talk again until they’ve both cleaned their plates, but Stiles does keep catching Derek’s eye, grinning before looking back down at his food. A few times he even blushes. Derek honestly doesn’t know what to do with it all, but he goes along with it because it makes him feel more pleasant than he has in a long time.

“I should get ready for work,” Derek says eventually, after they’ve both finished and have been staring at each other for just a bit too long.

Stiles nods once and agrees, “I have class in a couple of hours. Drop me off at my apartment before you head in?”

“Do you want the first shower, or me?” Derek asks instead of answering because it’s a stupid question. It’s not like he’s going to abandon Stiles to walk.

“Me,” Stiles decides immediately. “You know you always use all the hot water. What kind of question even is that?”

So they shower in turn, and brush their teeth side by side before heading out twenty minutes ahead of schedule. The whole thing makes something warm and unfamiliar settle low in Derek’s chest.

When he pulls up next to Stiles’ jeep, Stiles leans over the console to give Derek an achingly soft kiss and press their foreheads together for a second. Suddenly, everything clicks.

“See ya,” Stiles waves briefly, shutting the door behind him and turning away to unlock his own door.

Derek watches Stiles drive off. He's ten minutes late to work.

* * *

Derek is so lost in thought about what his life has become that he almost doesn’t notice Stiles’ dad come in the door at three.

“Afternoon, Derek,” the sheriff nods as he passes Derek’s desk. “How are you?”

“I think I’m in love with your son,” Derek blurts out. He quickly bangs his forehead against his desk to wallow in his own shame.

The sheriff lets out a choked noise that sounds suspiciously like he’s trying not to laugh. He’s heard Stiles make the same sound countless times before.

“What would you like me to do about that?”

Not lifting his head, Derek asks, “Can you just do me a solid and pretend that never happened?”

The sheriff barks out a laugh at that. “Not a chance in hell, kid.” Then, softer, “If you want my permission, you have it. But I don’t know how much good it’ll do you, since it’s not really me you have to go through.”

Derek looks up finally, and is met with a kind, if exasperated, expression.

“I told my wife’s brother that I was going to marry her before I ever even asked her out, if that helps.”

Oddly, it does.

“Thanks, Sheriff. Sorry, I’m a bit-“

“Don’t worry about it,” the sheriff cuts in, taping his knuckles on the desk twice before striding back to his office.

Derek’s head hits his desk again three minutes later when he remembers what he just did.

“Stop getting your feelings on the paperwork,” the sheriff calls out, amused. Derek just groans.

* * *

“Why did you ask me to get you a date last weekend?” Derek asks. Apparently it’s becoming a habit of his to demand things of Stiles before he can fully open the door.

Stiles blinks, and says, “I’m fine, and how are you?”

Rolling his eyes, Derek pushes past him into the living room. He doesn’t sit, just turns on his heel to face Stiles again. The younger man shuts his door, and leans back against it.

“Uh, I told you. I was sick of being alone, and I had been feeling weird for a while. I’m pretty sure that was because I was kind of into you and just hadn’t realized yet. I didn't have some nefarious plot to make you jealous or anything, if that's what you're thinking,” Stiles shrugs like it costs him nothing to admit it. He's also had days to figure it all out, though, whereas Derek has only had about ten hours to process.

When Derek doesn’t offer anything else, Stiles sighs, “Is this where you tell me we can’t do this? Or you don’t want this? Because that shit won’t fly with me. We both know I have a history of digging my claws into someone, pun intended. Also, you clearly want this just as much as I do. Pretty sure you had it figured out before I did. Speaking of, when _did_ you figure it out?”

“I,” Derek’s brow furrows, “this morning?”

“Bullshit,” Stiles laughs. When Derek doesn’t so much as crack a smile, he stops, surprised. “Wait, seriously? But you kept sabotaging my dates. Literally no one is that bad at being a wingman.”

“It’s not that easy,” Derek says defensively. “You try it, and see how you do.”

Stiles’ eyes widen slightly before he bursts out laughing. “Oh my god, this is the best thing that has ever happened to me.”

Derek folds his arms over his chest. It’s hard to stay testy when Stiles is so openly gleeful, so he lets go and smiles slightly. He catalogues the other man’s flushed face, and shining eyes when he finally calms down.

“Man, I love you,” Stiles shakes his head fondly. “Kind of wish I had realized it sooner. Kind of wish _you_ had realized it sooner. Last night could have gone way better.” He waggles his eyebrows playfully. It makes him look ridiculous, but Derek walks over to him anyway.

“I think last night went just fine,” Derek whispers, breath ghosting out against Stiles’ lips.

“Sap,” Stiles murmurs as he presses their lips together.

**Author's Note:**

> My headcanon is that Derek's apron was a gag gift, but he loved it so much no one had the heart to tell him. 
> 
> So, there's a chance I got the idea for this (hint, I most definitely got the idea for this) when I was reading this [matchmaking rec list](http://swingsetindecember.tumblr.com/post/59434098411/jens-matchmaking-dating-sterek-fic-recs). Credit where credit is due and all that. Hope it's okay that I ran with your suggestion!
> 
> Also, this is un-beta'd, so let me know if I've missed a mistake (or, you know, you feel like being hit up as a beta in the future because I don't currently have one)? Constructive criticism is also 100% welcome.
> 
> And, finally, you're welcome to come fine me on [tumblr](http://kirayaykimura.tumblr.com/) if you find yourself with a burning need.


End file.
